Cyclopropanecarboxylic acid, 2-formyl-3-[(phenylmethoxy)methyl]-, methyl ester, (1S,2S,3R)-

Base Information

• Chemical Name: Cyclopropanecarboxylic acid, 2-formyl-3-[(phenylmethoxy)methyl]-, methyl ester, (1S,2S,3R)-
• CAS No.: 653598-80-2
• Molecular Formula: C14H16O4
• Molecular Weight: 248.279
• Mol file: 653598-80-2.mol

Synonyms:

Chemical Property of Cyclopropanecarboxylic acid, 2-formyl-3-[(phenylmethoxy)methyl]-, methyl ester, (1S,2S,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopropanecarboxylic acid, 2-formyl-3-[(phenylmethoxy)methyl]-, methyl ester, (1S,2S,3R)-

There total 10 articles about Cyclopropanecarboxylic acid, 2-formyl-3-[(phenylmethoxy)methyl]-, methyl ester, (1S,2S,3R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

methyl (1R,2R,3S)-2-benzyloxymethyl-3-hydroxymethylcyclopropane carboxylate (653598-79-9) → methyl (1S,2S,3R)-3-benzyloxymethyl-2-formylcyclopropane carboxylate (653598-80-2)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃;

DOI:10.1021/jm030967o

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → methyl (1S,2S,3R)-3-benzyloxymethyl-2-formylcyclopropane carboxylate (653598-80-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / AcONa / tetrahydrofuran / 0.5 h / Heating

2: Et₃N; p-acetamidobenzenesulfonyl azide / acetonitrile / 2.5 h / 20 °C

3: 3.7 g / aq. LiOH / acetonitrile / 20 °C

4: 65 percent / Rh₂(4S-MPPIM)4 / CH₂Cl₂ / Heating

5: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

6: 0.65 g / diethyl ether / 1 h / 0 °C

7: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

8: KHMDS / tetrahydrofuran; toluene / 2.67 h / -78 - -10 °C

9: 0.22 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

10: 89 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 20 °C

With 1H-imidazole; lithium hydroxide; tetrapropylammonium perruthennate; Rh₂(4S-MPPIM)4; 4-acetamidobenzenesulfonyl azide; tetrabutyl ammonium fluoride; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm030967o

Reference yield:

diazoacetic acid 4-benzyloxy-but-2-enyl ester (181310-22-5) → methyl (1S,2S,3R)-3-benzyloxymethyl-2-formylcyclopropane carboxylate (653598-80-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / Rh₂(4S-MPPIM)4 / CH₂Cl₂ / Heating

2: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

3: 0.65 g / diethyl ether / 1 h / 0 °C

4: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

5: KHMDS / tetrahydrofuran; toluene / 2.67 h / -78 - -10 °C

6: 0.22 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

7: 89 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 20 °C

With 1H-imidazole; lithium hydroxide; tetrapropylammonium perruthennate; Rh₂(4S-MPPIM)4; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm030967o

upstream raw materials:

methyl (1R,2R,3S)-2-benzyloxymethyl-3-hydroxymethylcyclopropane carboxylate

(Z)-4-benzyloxy-but-2-en-1-ol

diazoacetic acid 4-benzyloxy-but-2-enyl ester

(1R,5S,6R)-6-(benzyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one

Downstream raw materials:

(2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile

ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate